3-Bromopropionic acid → (2-Carboxyethyl)triphenylphosphonium bromide

Participants

Reaction Steps

A solution of 90 g. (0.343 mole) of triphenylphosphine and 50 g. (0.326 mole) of 3-bromopropionic acid in 550 ml. of acetonitrile was refluxed for two days. The reaction mixture was then distilled under reduced pressure to remove acetonitrile, and the residue was stirred well together with diethyl ether, and then the upper ethereal layer removed by decantation. The operation was repeated twice to form the crystalline product, which was recrystallised from acetonitrile; yield of the title compound: 115 g, m.p. 195°-198°C. Infra-red (hereinafter abbreviated to IR) absorption spectrum (potassium bromide tablet): 2880, 1740, 1434, 1382, 1322, 1230, 1105, 745, 690, 520 and 505 cm-1.

Provenance & Evidence